EXPERIMENT 8 PREPARATION OF CYCLOHEXENE FROM CYCLOHEXANOL

OBJECTIVE

Synthesis of cyclohexene from cyclohexanol via water elimination with acid catalysed.

PRE-LAB ASSIGNMENT

1) Find the density for cyclohexanol and cylohexene. State the reference(s).

Cyclohexanol = 0.9624 g/cm3

Cyclohexene = 0.81 g/cm3

2) Show the calculation for the mass and moles for 20 ml of cyclohexanol.

Molecular formula of cyclohexanol = C6H120

Mass = 20 mL (0.9624 g/cm3 x 1 cm/mL)

= 19.248 g

Relative Molar Mass = 6(12) + 12 (1) + 16

= 100 g/mol

No. of mol = mass / RMM

= 19.248 g - 100 g/mol

= 0.1924 mol of cyclohexanol

PREREQUISITE

1) Techniques as in experiment 1 will be required in experiment 8.

INTRODUCTION

Alcohols undergo elimination reaction in the presence of a strong acid to form an

alkene. Strong acids such as Phosphoric acid (H3PO4) are used in the dehydration reaction of
alcohols. The acid needs to protonate the -OH group because -OH is a strong base making it a
poor leaving group. Once the -OH has been protonated to H20, it can leaves and the
nucleophile will obstruct a beta hydrogen to form an alkene. In this experiment, cyclohexanol
is dehydrated to cyclohexene in the presence of concentrated phosphoric acid. Distillation is
employed in this experiment to synthesize and purify cyclohexene. The principle of
distillation as a separation method is based on the difference in boiling points of substances.
Cyclohexanol is a secondary saturated alcohol with boiling point of 100.16°C which
undergoes elimination reaction to form cyclohexene.

METHODS

1. Set up a simple distillation apparatus.

2. Add around 10-11.5ml of 85% phosphoric acid in a round bottom flask.

3. Add in 20 ml of cyclohexanol and a few boiling chips.

4. Distill the reaction mixture.

5. Immerse the receiving flask up to its neck in an ice bath to avoid loss of any product (b.p.
83°C).

6. Heat the distillation flask carefully so that a steady distillation rate is obtained.

7. Do not allow the temperature of the distilling vapors to exceed 103 C. Stop heating the
reaction mixture when only a few ml of liquid remains in the distilling flask or when the
vapors exceed 103°C.

8. Saturate the distillate by adding solid sodium chloride portion wise with swirling

(Note: stop adding the salt when it is not dissolved anymore). Try to keep the excess sodium
chloride to a minimum.

9. Now, neutralize any acid by adding just enough 10% sodium carbonate (Na2CO3(aq))
solution to the mixture with swirling to make the aqueous layer basic (use blue litmus paper
to the solution). Note: every a few drops of Na2CO3(aq) added, test the solution by putting a
drop of the solution on a blue litmus paper until it the blue litmus paper remained blue.

10. Transfer the mixture to a separatory funnel and drain of the aqueous layer. At this stage
you need to determine yourself which layer is aqueous using the technique you learned in
experiment 1.

11. Pour the organic layer into an Erlenmeyer/conical flask and dry it with just enough
anhydrous magnesium sulfate.

12. Filter the product into a clean, dry, round bottom flask via gravity filtration.

13. Redistill the dried cyclohexene.

14. Record the boiling point and measure the volume of the product.

15. Test the product form with a few drops of KMnO4(aq), observe the colour change.

QUESTIONS

1) Find the moles of cyclohexene formed in the experiment.

Volume from the experiment = 10ml Molar mass of cyclohexene = 82.143g/mol

Density of cyclohexene = 0.81g/ml

Mass of cyclohexene = volume x density

= 10ml x 0.81g/ml =8.10g

Moles of cyclohexene = mass/molar mass

= 8.10g - 82.143g/mol =0.09861mol of cyclohexene

2) Calculate the expected mass of pure product cyclohexene using the number of moles
cyclohexanol used in the experiment based on the equation.

1mole cyclohexanol = 1 mole cyclohexene

Expected mass of cyclohexene = mole x molar mass

= 0.1924mol x 82.143g/mol

= 15.8043g of cyclohexene
3) Show the calculation for the percentage yield/conversion of cyclohexanol to cyclohexene.

Percentage yield = (experimental mass/theoretical mass)/100

= (8.10g/15.80)/100 = 51.27% of cyclohexene

4) Suggestion another simple chemical test for the product instead of KMnO4(aq) and state
the

observation.

A simple chemical test can be used is with the bromine water, it will tell the difference
between an alkane and an alkene as it will decolourise the colour of bromine water.

5) Draw the products that would be obtained by the dehydration of the following molecules
and state which are minor and major products.

(a) 2-heptanol

(b) 2-methyl-1-cyclohexanol

6) Why the amount of 85% phosphoric acid is not necessarily to be exact amount as
cyclohexanol?

This is because the phosphoric acid only act as a catalyst in the process which the function is
to speed up the reaction.
RESULTS

Boiling point of cyclohexene = 80°C

Volume of the product (cyclohexanol) = 10ml

Before KMnO4 added Clear colour of cyclohexanol.

After KMnO4 added Purple colour of KMnO4 truns the product
into brown colour.

DISCUSSION

In this experiment, cyclohexanol was synthesized to cyclohexene via distillation and

extraction. The clear colour of 85% phosphoric acid was added to cyclohexanol in a round
bottom flask in this experiment, which act as catalysts to have the dehydration reaction then
would yield to the cyclohexene. The solution then was immersed into the ice bath to avoid
the product evaporated. Then, the distillation process was conducted to obtain the distillate of
cyclohexene by make sure the temperature of distilling vapors not exceed to 103C. The
solution in the round bottom flask was heated carefully to get a steady distillation rate. Then,
the distillate product was saturated by adding the sodium chloride to the mixture then it formt
a two layer of clear solution. The solution then was neutralized by addition of 2 drops sodium
carbonate and it was tested with the blue litmus paper which the blue litmus paper is remains.
It showed that the aqueous layer is in a base condition.

Next, the solution was transferred into the separating funnel. Two layers form in this
condition which aqueous layer is on the bottom while the organic layer in on the top. The
lower aqueous layer was discarded while the upper organic layer was decanted to a conical
flask. Then, enough amount of anhydrous sodium sulfate was placed in solution. Since the
anhydrous sodium sulphate is a very good dehydrating agent, it was used to remove the water
in the mixture with cyclohexene. As the excess amount of anhydrous sodium sulphate was
into the mixture, the water can be absorbed by it while the remains are the cyclohexene with
the rest of the anhydrous sodium sulphate solid. After filtration, the remained dehydrating
agent was filtered out, so the dry organic cyclohexene was obtained.

From the second distillation, the percentage yield of cyclohexene is around 51.27%.
The cyclohexene was distillated to cyclohexanol which the boiling point of the product is
80C and the volume of the product was obtained is 10ml. The product is in a clear liquid
condition after distillation process. Then, the solution was tested with a few drops of
KMnO4(aq) which turns the purple colour of KMnO4 to the brown colour. Therefore, this
solution was accepted as cyclohexanol where the colour of KMnO4 turn to brown when
tested with alcohol.

CONCLUSION

As a conclusion, the synthesis of cyclohexene from cyclohexanol via water

elimination with acid catalyst was identified which the volume of the cyclohexanol is 10ml
and the percentage yield of the cyclohexene is 51.27%. This synthesis process had been done
by the distillation and extraction techniques. This experiment can be accepted.